5655-61-8

Basic information

• Product Name: L-BORNYL ACETATE
• Synonyms: 1,7,7-trimethyl-,acetate,(1s-endo)-bicyclo[2.2.1]heptan-2-o;1,7,7-trimethyl-,acetate,(1S-endo)-Bicyclo[2.2.1]heptan-2-ol;Bicyclo[2.2.1]heptan-2-ol,1,7,7-trimethyl-,acetate,(1S-endo)-;Borneol, acetate, (1S,2R,4S)-(-)-;L-alpha-bornyl acetate;Levo-bornyl acetate;BORNYL ACETATE, L-;ENDO-(1S)-1,7,7-TRIMETHYLBICYCLO[2.2.1]HEPT-2-YL ACETATE
• CAS NO: 5655-61-8
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• EINECS: 243-750-6
• Product Categories: Bicyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 5655-61-8.mol

Chemical Properties

• Melting Point: 27°C
• Boiling Point: 223-224 °C(lit.)
• Flash Point: 184 °F
• Appearance: Clear colorless/Liquid
• Density: 0.984g/mL20°C
• Vapor Pressure: 0.6 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.463
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: 62.6mg/L at 20℃
• Merck: 14,1339
• BRN: 2502036
• CAS DataBase Reference: L-BORNYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: L-BORNYL ACETATE(5655-61-8)
• EPA Substance Registry System: L-BORNYL ACETATE(5655-61-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 23-24/25-36-26
• RIDADR: NA 1993 / PGIII
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 5655-61-8(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
L-BORNYL ACETATE is used as a flavoring agent for its lemon-like aroma, adding a fresh and citrusy note to food products and beverages. It is also used as a fragrance ingredient in perfumes, soaps, and cosmetics, providing a pleasant and refreshing scent.
Used in Pharmaceutical Industry:
L-BORNYL ACETATE is used as a key intermediate in the synthesis of camphor, a widely used compound with various medicinal properties. Camphor has been traditionally used as a stimulant, anti-inflammatory, and analgesic agent.
Used in Cancer Research:
L-BORNYL ACETATE is used in the preparation of (-)-englerin A, a promising anti-cancer agent. (-)-Englerin A has shown potential in targeting cancer cells by disrupting their energy metabolism and inducing cell death, making it a valuable compound in the development of novel cancer therapies.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10+,12+/m1/s1

Upstream product

• 464-41-5 bornyl chloride 
• 557-34-6 zinc diacetate 
• 464-45-9 endo-borneol 
• 108-24-7 acetic anhydride 
• 464-43-7 d-borneol 
• 13429-40-8 camphene hydrate 
• 64-19-7 acetic acid 
• 18172-67-3 beta-pinene 
• 7785-70-8 (+)-α-pinene 
• 542-16-5 dianilunium sulphate 
• 464-17-5 (+-)-bornylene 
• 565-00-4 dl-camphene 
• 80-56-8 rac-α-pinene 
• 127-09-3 sodium acetate 

Downstream Products

• 91839-99-5 dl-6-acetoxy-bornan-3-one 
• 76-22-2 Camphor 
• 39850-78-7 5-Ketoborneol 
• 565-00-4 dl-camphene 
• 4680-20-0 2-(5,5,6-trimethylbicyclo[2.2.1]hept-exo-2-yl)phenol 
• 74-85-1 ethene 
• 464-17-5 1,7,7-trimethylbicyclo[2.2.1]hept-2-ene 
• 508-32-7 1,7,7-trimethyltricyclo[2.2.1.02,6]heptane 
• 79-92-5 camphene 
• 4249-09-6 1,5,5-trimethyl-cyclopenta-1,3-diene 
• 64-19-7 acetic acid 
• 464-45-9 endo-borneol 
• 54717-80-5 bornyl acetoacetate 
• 10359-41-8 2α,5β-dihydroxybornane 

Relevant articles and documents

Simple Plug-In Synthetic Step for the Synthesis of (?)-Camphor from Renewable Starting Materials

Racemic camphor and isoborneol are readily available as industrial side products, whereas (1R)-camphor is available from natural sources. Optically pure (1S)-camphor, however, is much more difficult to obtain. The synthesis of racemic camphor from α-pinene proceeds via an intermediary racemic isobornyl ester, which is then hydrolyzed and oxidized to give camphor. We reasoned that enantioselective hydrolysis of isobornyl esters would give facile access to optically pure isoborneol and camphor isomers, respectively. While screening of a set of commercial lipases and esterases in the kinetic resolution of racemic monoterpenols did not lead to the identification of any enantioselective enzymes, the cephalosporin Esterase B from Burkholderia gladioli (EstB) and Esterase C (EstC) from Rhodococcus rhodochrous showed outstanding enantioselectivity (E>100) towards the butyryl esters of isoborneol, borneol and fenchol. The enantioselectivity was higher with increasing chain length of the acyl moiety of the substrate. The kinetic resolution of isobornyl butyrate can be easily integrated into the production of camphor from α-pinene and thus allows the facile synthesis of optically pure monoterpenols from a renewable side-product.

Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives

Insight into the mechanism of a safe, simple, and inexpensive phosphoric acid (H3PO4)-catalyzed acylation of alcohols with acid anhydrides is described. The corresponding in situ-generated diacylated mixed anhydrides, unlike traditionally proposed monoacylated mixed anhydrides, are proposed as the active species. In particular, the diacylated mixed anhydrides act as efficient catalytic acyl transfer reagents rather than as Br?nsted acid catalysts simply activating acid anhydrides. Remarkably, highly efficient phosphoric acid (1-3 mol %)-catalyzed acylation of alcohols with acid anhydrides was achieved and a 23 g scale synthesis of an ester was demonstrated. Also, phosphoric acid catalyst was effective for synthetically useful esterification from carboxylic acids, alcohols, and acid anhydride. Moreover, with regard to recent developments in chiral 1,1′-bi-2-naphthol (BINOL)-derived phosphoric acid diester catalysts toward asymmetric kinetic resolution of alcohols by acylation, some phosphate diesters were examined. As a result, a 31P NMR study and a kinetics study strongly supported not only the acid-base cooperative mechanism as previously proposed by other researchers but also the mixed anhydride mechanism as presently proposed by us.

Method for synthesizing bornyl acetate from turpentine

The invention discloses a method for synthesizing bornyl acetate from turpentine, which relates to the technical field of deep processing of turpentine. The preparation method comprises the followingsteps of proportioning titanium sulfate and hydroxycarboxylic acid to form a composite catalyst, mixing turpentine, acetic acid and the composite catalyst, and reacting in a stirring state, after thereaction is finished, filtering, and removing acetic acid from the filtrate to obtain a solution containing bornyl acetate, neutralizing the solution containing the bornyl acetate, and washing with water to obtain a bornyl acetate crude product, and then fractionating the crude product of the bornyl acetate to obtain the bornyl acetate. The synthesis method provided by the invention is high in catalytic activity, low in cost and high in selectivity on the borneol acetate, and does not need to use a raw material with too high pinene content.

Manganese-mediated acetylation of alcohols, phenols, thiols, and amines utilizing acetic anhydride

Manganese(II) chloride-catalyzed acetylation of alcohols, phenols thiols and amines with acetic anhydride is reported. This method is environment-friendly and economically viable as it involves inexpensive, relatively benign catalyst, mild reaction condition, and simple workup. Acetylation is performed under the solvent-free condition at ambient temperature and acetylated products obtained in good to excellent yields. Primary, secondary heterocyclic amines, and phenols with various functional groups are smoothly acetylated in good yields. This method exhibits exquisite chemoselectivity, the amino group is preferentially acetylated in the presence of a hydroxyl/thiol group.

Heterogeneous zeolite-based catalyst for esterification of α-pinene to α-terpinyl acetate

The purpose of this study is to determine the most effective type of heterogeneous catalyst such as natural zeolite (ZA), Zr-natural zeolite (Zr/ZA) and zeolite Y (H/ZY) in esterification of α-pinene. α-terpinyl acetate was successfully synthesized from α-pinene and acetic anhydride by their heterogeneous catalysts. The esterification reaction was carried out with reaction time, temperature and zeolite catalysts. The most effective catalysts used in the synthesis of α-terpinyl acetate is catalyst H/ZY with the yield is 52.83% at 40oC for the time 4 h with a selectivity of 61.38%. The results showed that the effective separation of catalyst could contribute to developing a new strategy for the synthesis of α-terpinyl acetate.

Method for synthesizing isobornyl acetate by camphene

The invention discloses a method for synthesizing isobornyl acetate by camphene. The method comprises the following steps of adding camphene, glacial acetic acid, a main catalyst (hydroxycarboxylic acid) and an additive into a reaction kettle according to a mass ratio of 100:(20 to 400):(1 to 50):(1 to 20), starting to stir, controlling the temperature to 40 to 100 DEG C, and reacting for 2 to 24h, so as to obtain a synthesized product; adding a small amount of water into the synthesized product, standing and delaminating, wherein the upper oil layer is a target product containing isobornyl acetate, the lower layer is acid water containing the catalyst and acetic acid, and the acid water is dewatered and recycled; adding the target product into a water washing tank, adding alkaline water to neutralize, and then adding water to wash, so as to obtain a crude product of the isobornyl acetate; relieving pressure and distilling, so as to obtain the refined isobornyl acetate. The method forsynthesizing the isobornyl acetate by catalyzing the camphene has the advantages that the obtained product has high yield and high purity, and is easy to separate; the used catalyst has high catalyzing activity; the preparation is simple, the repeatability is good, the toxicity is avoided, the corrosion property is low, the isobornyl acetate belongs to regeneration resources, and the industrialization product is easy.

Method for catalyzing alpha-pinene ethyl esterification by using glutamic-acid-functionalized phosphotungstic acid dihydric salt

The invention relates to an alpha-pinene ethyl esterification reaction method, particularly a method for catalyzing alpha-pinene ethyl esterification reaction by using acid-salt-structure glutamic-acid-functionalized phosphotungstic acid dihydric salt, belonging to the technical field of biomass catalytic conversion. The catalytic esterification capacity of the two carboxyl functional groups in the glutamic acid cations and the acid catalysis capacity of the acid salt protons in the acid-salt-structure glutamic-acid-functionalized phosphotungstic acid dihydric salt [Glu]H2PW12O40 are utilized to implement alpha-pinene one-step ethyl esterification reaction under the condition of no other cocatalysts. After the catalytic reaction finishes, standing is performed, the supernatant esterification product phase only needs a small amount of water for washing, thereby greatly reducing the wastewater generation as compared with the industrial sulfuric acid catalysis process and chloroacetic acid assisted catalysis process. The catalyst which is insoluble in the organic phase can be directly recycled only after simple drying treatment.

Rice husk ash: A new, cheap, efficient, and reusable reagent for the protection of alcohols, phenols, amines, and thiols

Amild, efficient, and eco-friendly protocol for the protection of alcohols and phenols as trimethylsilyl ethers has been developed using rice husk ash as a reagent. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols, and amines with acetic anhydride. All reactions were performed under mild conditions in good to high yields. Copyright

Oxidation of α-pinene by atmospheric oxygen in the supercritical CO2-ethyl acetate system in the presence of Co(II) complexes

The reactivity of monoterpene α-pinene in a flow reactor in the presence of cobalt catalyst in a complex supercritical solvent consisting of CO2 and ethyl acetate is studied over the temperature range of 190-320°C and a pressure range of 110-125 atm. It was found that the main isomerization products include compounds with bicyclo[2.2.1]heptane and p-menthane backbones; the reaction is accompanied by partial racemization. The formation of oxidation products is observed in the presence of air, with epoxydation rather than allylic oxidation being the predominant process at the first stage. The oxidized products (campholenic aldehyde, verbenone, pinocamphone) are shown to be formed with a high enantioselectivity; the formation of acetoxylation products is observed at temperatures above 200°C.